Synonym
Immethridine 2HBr, Immethridine (hydrobromide), Immethridine dihydrobromide
IUPAC/Chemical Name
4-((1H-imidazol-4-yl)methyl)pyridine dihydrobromide
InChi Key
CYNKWHIKNDIVDR-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H9N3.2BrH/c1-3-10-4-2-8(1)5-9-6-11-7-12-9;;/h1-4,6-7H,5H2,(H,11,12);2*1H
SMILES Code
[H]Br.[H]Br.C1(CC2=CC=NC=C2)=CNC=N1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Immethridine dihydrobromide does not bind to H1 or H2 receptors at concentrations up to 10 μM.
Biological target:
Immethridine dihydrobromide is a potent and highly selective histamine H3 receptor agonist (pEC50 = 9.74) that displays 300-fold selectivity over the H4 receptor (pKi values are 9.07 and 6.61 respectively).
In vitro activity:
The data showed that immethridine-treated DCs had lower expression level of IL-6, TGF-β and IL-12 P40 compared to PBS (Figure (Figure 3A), and the data were confirmed by Q-PCR (Figure 3B) and ELISA (Figure 3C). Taken altogether, these results suggested that immethridine could inhibit cytokine production in DCs.
Reference: Oncotarget. 2017 Aug 24;8(43):75038-75049. https://pubmed.ncbi.nlm.nih.gov/29088843/
In vivo activity:
The Imm (Immethridine) treatment attenuated the ventricular interstitial fibrosis observed in the Sirius-red staining and the increased expression of the collagen type I α 1 gene in the hearts of ANS mice (SI Appendix, Fig. S2 D and E).
Reference: Proc Natl Acad Sci U S A. 2020 Feb 11;117(6):3150-3156. https://pubmed.ncbi.nlm.nih.gov/31992639/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Water |
32.1 |
100.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
321.02
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Shi Y, Li Z, Chen R, Zhang J, Hu X, He C, Su Q, Ma H, Ren H, Qian M, Cui S, Jiang W. Immethridine, histamine H3-receptor (H3R) agonist, alleviated experimental autoimmune encephalomyelitis via inhibiting the function of dendritic cells. Oncotarget. 2017 Aug 24;8(43):75038-75049. doi: 10.18632/oncotarget.20500. PMID: 29088843; PMCID: PMC5650398.
2. Noguchi K, Ishida J, Kim JD, Muromachi N, Kako K, Mizukami H, Lu W, Ishimaru T, Kawasaki S, Kaneko S, Usui J, Ohtsu H, Yamagata K, Fukamizu A. Histamine receptor agonist alleviates severe cardiorenal damages by eliciting anti-inflammatory programming. Proc Natl Acad Sci U S A. 2020 Feb 11;117(6):3150-3156. doi: 10.1073/pnas.1909124117. Epub 2020 Jan 28. PMID: 31992639; PMCID: PMC7022214.
3. Adami M, Pozzoli C, Leurs R, Stark H, Coruzzi G. Histamine H(3) receptors are involved in the protective effect of ghrelin against HCl-induced gastric damage in rats. Pharmacology. 2010;86(5-6):259-66. doi: 10.1159/000320110. Epub 2010 Oct 22. PMID: 20975320.
In vitro protocol:
1. Shi Y, Li Z, Chen R, Zhang J, Hu X, He C, Su Q, Ma H, Ren H, Qian M, Cui S, Jiang W. Immethridine, histamine H3-receptor (H3R) agonist, alleviated experimental autoimmune encephalomyelitis via inhibiting the function of dendritic cells. Oncotarget. 2017 Aug 24;8(43):75038-75049. doi: 10.18632/oncotarget.20500. PMID: 29088843; PMCID: PMC5650398.
In vivo protocol:
1. Noguchi K, Ishida J, Kim JD, Muromachi N, Kako K, Mizukami H, Lu W, Ishimaru T, Kawasaki S, Kaneko S, Usui J, Ohtsu H, Yamagata K, Fukamizu A. Histamine receptor agonist alleviates severe cardiorenal damages by eliciting anti-inflammatory programming. Proc Natl Acad Sci U S A. 2020 Feb 11;117(6):3150-3156. doi: 10.1073/pnas.1909124117. Epub 2020 Jan 28. PMID: 31992639; PMCID: PMC7022214.
2. Adami M, Pozzoli C, Leurs R, Stark H, Coruzzi G. Histamine H(3) receptors are involved in the protective effect of ghrelin against HCl-induced gastric damage in rats. Pharmacology. 2010;86(5-6):259-66. doi: 10.1159/000320110. Epub 2010 Oct 22. PMID: 20975320.
1: Shi Y, Li Z, Chen R, Zhang J, Hu X, He C, Su Q, Ma H, Ren H, Qian M, Cui S, Jiang W. Immethridine, histamine H(3)-receptor (H(3)R) agonist, alleviated experimental autoimmune encephalomyelitis via inhibiting the function of dendritic cells. Oncotarget. 2017 Aug 24;8(43):75038-75049. doi: 10.18632/oncotarget.20500. eCollection 2017 Sep 26. PubMed PMID: 29088843; PubMed Central PMCID: PMC5650398.
2: Kitbunnadaj R, Zuiderveld OP, Christophe B, Hulscher S, Menge WM, Gelens E, Snip E, Bakker RA, Celanire S, Gillard M, Talaga P, Timmerman H, Leurs R. Identification of 4-(1H-imidazol-4(5)-ylmethyl)pyridine (immethridine) as a novel, potent, and highly selective histamine H(3) receptor agonist. J Med Chem. 2004 May 6;47(10):2414-7. PubMed PMID: 15115383.
